What If? The Pleasantville Strangler
by Aris1013
Summary: What if Merton did fall down the well and it sent him and Tommy back in time to when the Strangler was attacking? Tommy and Merton will have to figure out how to get back to the present while dealing with the Pleasantville Strangler. One-Shot.


_**Normal POV**_

After Merton had given his speech about the Pleasantville Strangler in class, he was determined to prove to everyone that the well did exist and was underneath the school. He found blueprints of the town from the 1880's and compared them to the current blueprints, and saw that he was right. It only took Merton a few minutes to grab supplies and head out in search of Tommy, he knew it was time to uncover this well and prove he was right. As soon as Merton found Tommy he dragged him down to the basement where he thought the well was. There was already a crack in the floor so Merton decided to use it to start digging.

"Let the excavation begin." Merton slammed his pickaxe into the crack and felt the shockwave go all the way up his body causing him to shake into the lockers and then into Tommy.

"Okay, okay, uhm, I'm gonna head into the daylight now so…" Tommy began to walk away thinking Merton was insane for thinking there was actually a well in the basement.

"Wait." Merton held out his hand. "Did you hear that?"

"Hear what?" Tommy rolled his eyes, but then he heard a loud cracking noise and Merton scream. "Merton!"

Well Merton was right; there was a well right where Merton had been standing, and now all Tommy could see was the darkness of the long tunnel below. The weird thing about Merton falling though was that Tommy never heard him hit the bottom, which either meant the well went down extremely far, or Merton managed to grab onto to something on the way down.

"Merton! Merton, can you hear me?" No answer. What was Tommy going to do? He looked around until he found some rope that Merton had brought with him. He found a pipe to tie the rope around and started to climb down. "I'm coming buddy!"

Tommy climbed down hoping to find an alright Merton soon. As he climbed down he started to hear a weird noise coming from rope. Uh oh…the rope gave a little and Tommy tried to grab onto the slimy sides of the well with no luck. The rope snapped and Tommy began to fall. Tommy thought he would hit the waters soon, but he just continued to fall and fall, this well must have been a lot deeper than he thought. Instead of a splash, Tommy seemed to roll out of the well and onto the ground, which was very confusing.

"What the?" Tommy looked around realized he was not in the school basement anymore, but in the middle of a town square.

"Tommy!" Merton ran over to the disoriented Tommy with a big goofy smile on his face.

"Merton! What happened? Where are we?" This place looked a lot different than the Pleasantville he was used to.

"I think we got sent back to 1888, the year the Pleasantville Strangler got pushed down the well!"

Tommy's eyes widened. "What!? Merton you have to get us out of here."

"But Tommy don't you see, we have a chance to take in all the history of Pleasantville over a hundred years ago, imagine the things we could discover, imagine the thing we could invent before other people do."

Tommy saw that money hungry look in Merton's eyes. "Merton we aren't going to change anything here, you should know better than anyone if we mess with the past it could screw up the present, haven't you seen Back to the Future?"

Merton sighed. "Yeah you're right. Hmm, now to figure out how to get out of here." Merton paced around as the sun was setting on Pleasantville. "Ah ha!"

"What, did you figure it out?" Tommy took a step towards Merton.

Merton was looking at the well. "Maybe. We could try jumping into the well and hope that it sends us back to our time."

"Great, let's do it." Tommy clapped his hands together and made his way towards the well.

"But! It could also send us into a watery grave." Merton gave an innocent smile.

"Then what are we supposed to do?"

Before Merton could answer they heard a scream from down the street. The two boys looked at each other and ran towards the scream. They came across an alley with two people in it. One was an older man who was attempting to strangle a young blonde woman. The boys stopped at the end of the alley.

"Tommy! It's the Pleasantville Strangler!" Merton smiled, wide eyed.

"Well I'm not going to let him almost strangle that lady." He growled a little and began to wolf out.

Tommy stomped up behind the Strangler and tapped him on the shoulder. The man turned around and looked horrified at the creature before him. Tommy punched him and he flew against the wall next to him. Tommy glared at him, and then went to help the woman the man was trying to strangler. The woman looked at Tommy in terror before giving a blood curdling scream louder than the one the boys had heard earlier. She pushed Tommy away and ran past him and Merton while screaming into the town.

"Help! Monster, monster!"

Merton walked over to Tommy. "Geez, what's her problem?"

Tommy scoffed. "I don't know, just seems some people can't accept help when they need it."

Merton nodded and then they heard a groan coming from the ground. The Strangler was getting up. He saw Tommy and gaped at him before crawling up the wall to stand up and shuffled out of the alley. Before the two boys could get out of the alley to follow the Strangler, the woman came back with the constable and other officers, and pointed at Tommy and Merton.

"Look at the monster! They tried to kill me!"

Tommy's eyes widened. "No, no the Strangler, he was here and I…" He looked at his paws and then put them behind his back. "Okay I know what this must look like, but I really think if we could just talk you'd see this all just one big misunderstanding…hey" He pointed at the constable. "Do I know you from somewhere?"

Merton looked at the constable then back at Tommy and realized the connection. He took a big step behind Tommy and whispered in his ear. "Tommy! I think this is your Great, Great Grandfather! He was the constable that pushed the Strangler down the well!"

"What, really? That's so cool." He held his hand out to his Grandfather. "Hey man I'm Tom-"

Constable Dawkins scowled at Tommy. "Detain those lads at once!" The men all looked horrified at Tommy, but began forward anyway.

"Oh, guess no family reunion, time to go!"

Tommy looked around and saw a fire escape on the building behind them. He grabbed Merton by the shoulder and hauled him up the ladder. They ran up to the top of the building and sprinted across the roof. There was another building close enough for them to jump, so Tommy grabbed Merton and jumped across the gap. Merton screeched as the tumbled onto the pavement. They got up and hid around the door that led downstairs to the rest of the building. Tommy put his paw over Merton mouth to keep his hyperventilating quite. He could hear his Grandfather searching the other roof before giving up and heading back down to the ground. Tommy let out a relieved breath and calmed himself down enough to turn back into a human.

"Tommy we may have just changed the past for the worst. They saw you and now they think we are the ones who have been hurting people, what if they throw us down the well and the Strangler just goes free? If he keeps at it, he may finally get the strength to actually strangle someone."

"Look, we aren't going to let that happen, we will get this all straightened out, we just have to figure out how."

The boys thought for a long time trying to come up with a plan to set things back in motion, but both were coming up short. A long time had passed before Merton finally perked up and snapped his fingers.

"I got it!"

Tommy was falling asleep, but perked up at Merton's excitement. "What?"

"Okay, you look just like your Great, Great Grandfather; so what if we find the Strangler, you pose as your Grandfather and we turn him in to set things straight once and for all!"

"Merton, I don't know about that. Where are we even gonna find the Strangler, and what if my Grandpa shows up while I'm acting like him?"

Merton thought for a moment and shrugged. "You got any better ideas?"

Tommy clapped his hands together. "Okay, one Strangler it is then."

"Uh huh." Merton nodded and the two boys left the roof in hopes of tracking down the Strangler.

The boys walked all over Pleasantville trying to stay out of site from the angry mobs looking for them, while also attempting to find the Strangler. The night grew darker and a fog set in over the quiet town. As they entered a cramped alley Tommy could tell Merton was beginning to feel uneasy, and if he were honest with himself he would admit that he felt a bit on edge as well. Neither boy knew for sure they would be able to get back to the present and that scared them.

"You know Tommy, maybe searching for the Strangler isn't such a good idea, maybe we should just wait this whole thing out and see if we get sent back to the future. Or! Maybe we could just live here, you know it wouldn't be so bad, sure there's not TV, or computers, or Goths yet, but hey it can't be that bad right?" Merton gave Tommy a nervous smile.

Tommy rolled his eyes. "We're gonna figure out how to get out of here Merton, but first we have to find what we are looking for."

"That would not happen to be me now would it?"

Tommy and Merton turned around to see the Pleasantville Strangler standing before them. He had a sinister smile on his face.

"See Merton, I told you we'd find him." Tommy had a confident smile on his face.

"Usually I'm the one to stalk people, but you two have made it much easier. Now who shall I start with first." He looked Tommy and Merton over. "Ah, how about the little one."

Merton choked a little stroking his neck and looked at Tommy.

"Hey! I'm not gonna let you choke anyone you got it!" Tommy pointed his finger at the Strangler.

"Hmm, we will have to see about that, oh…" The Strangler grabbed his chest and fell to one knee on the ground.

Since Tommy cared about others he walked up to the Strangler. "Hey man, are you alright?"

As soon as Tommy was close the Strangler sprang up and threw a brick at his head knocking Tommy to the ground. "Yes, as a matter of fact, I am quite well." He then looked at Merton and began to corner him.

Merton gave an uneasy laugh. "Okay, I know what you must be thinking, scrawny neck means easy to strangle, but I assure you my neck muscles are quite thick, in fact I-"

The Strangler grabbed Merton by the throat and shoved him against the wall. At first Merton struggled and let out dramatic choking noises, but soon enough they were replaced by giggles.

"Hey, that tickles." Merton continued to laugh while the Strangler attempted to strangle him.

The Strangler squeezed harder but Merton still giggled and squirmed. Soon the Strangler could hear growling behind him. He let go of Merton to see the werewolf standing behind him sneering.

"So it tis you that be the werewolf."

"That's right, I be the werewolf, and I'm taking you down." Tommy lunged at the Strangler.

Merton rolled his eyes at Tommy's sentence and moved out of the way so he could take the Strangler down. "Yeah, that's right Tommy you got him!"

Tommy tackled the Strangler to the ground and they rolled around a little before Tommy was able to restrain him. He hauled him up off the ground and smiled at his achievement.

"Alright Strangler, time to put a stop to your, uh, strangling." Tommy nodded and smiled.

Merton raised his finger up. "Attempted strangling."

"Whatever, what matters is, we got this guy, so we can finally get back home, hopefully." Tommy began to haul the Strangler into the town square, but Merton stopped him.

"Um, Tommy aren't you forgetting something."

Tommy looked at Merton confused.

Merton looked at Tommy for a moment to give him time to get it, but he did not seem to. "You know the whole…" Merton held up his fingers like fangs. "thing."

"Oh! Right." Tommy laughed and closed his eyes. He took slow breathes in and out until he turned back to normal. "Okay, Strangler, time to take you down."

They dragged the Strangler towards the angry mob that was searching for the werewolf. When they came across them Tommy was glad to not see his Great, Great Grandfather anywhere. The mob looked threatening though and Tommy was not sure if they would buy him posing as his Grandfather. He motioned for Merton to stay back a bit so no one recognized him from earlier and attempted to talk to the crowd.

"Everyone, this is your constable, um, Thomas P. Dawkins, and I uh caught the real criminal in all these strangulation attempts." He held out the Strangler who gave the crown a nervous smile.

The crowd studied Tommy for a moment. A random townsperson yelled at Tommy. "But what about the wolf?"

Tommy thought for a moment before answering. "That was just um, a dog! The real criminal is here he has been attempting to strangle the people of this town!"

Another townsperson studied the man in Tommy's hands. "That is the man that tried to strangle me! Get him!" The townspeople cheered and raised their torches and pitch forks. Yelling began as to what they should do with the Strangler, but someone yelled that they should throw him down the well and the crowd cheered. Tommy decided to shove the Strangler into the crowd and let them handle everything. He and Merton followed them to the well, hoping that his Grandfather never showed up. They all gathered around the well until a few guys shoved the struggling Strangler in front of the well.

He looked at Tommy. "You'll pay for this Thomas P. Dawkins! Mark my words!" With that the men holding him shoved the Strangler down the well and he fell to a watery grave.

Tommy turned to Merton. "Okay, everything is back the way it's supposed to be, so how do we get back?"

Merton looked as if he was going to say something useful then gave up. "I don't know."

"Great, now what?" Tommy threw his hands up.

Merton shrugged. "I don't kn-" Out of no where Merton seemed to be sucked up into the sky, but Tommy could not see him anymore.

"Merton?" Tommy looked around but did not see him. Soon after Merton disappeared, Tommy felt like he was falling again and everything when black.

Before he knew it, Tommy was laying on the basement floor where he and Merlin uncovered the well. He looked over and saw Merton slowly getting up, rubbing his shoulder from the hard fall. Tommy shook off his shakiness and got up as well.

"Woah, that was weird."

Merton nodded. "You're telling me." He looked at the well. "Tommy do you realize what this means!"

Tommy gave Merton a blank stare.

Merton sighed. "We are the first people to travel back in time!"

Tommy was looking at the well. "So what are we going to do about that, we can't just leave it out here like this."

"Hmm, I guess we should seal it back up." Merton stopped jumping in joy and looked at the gaping hole in the floor.

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_**Tommy's POV**_

Things finally got back to normal after we sent the Strangler down the well. I was a little worried the Strangler would come back or something after he cursed me, but we haven't heard a peep out of that well since. We had no other weird time travel experiences, especially after Merton and I sealed up the well, the Merton J. Dingle memorial well that is. He decided that since he discovered the well, it should be named after him. After we sealed the well Merton tried explaining to me why exactly we got sent back in time, but after an hour of rambling I was so lost I just nodded and moved on. He said something about reality ripping at the moment we were at the well, or something, but as long as it's all behind me I don't really care. I am just happy to be at home with the TV, even if Dean has to choose the channel.

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**AN: Thanks so much for reading! I hope you enjoyed this one, it was kind of stretch as my first idea ended up going no where. Thanks again for reading! **


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